Let’s be honest: Scheduling a meeting, an appointment, or even a coffee chat with a long-time friend can be a pain in the you-know-what. Your contact agrees to meet up, you propose three different times on three different dates, and—what do you know—your contact can’t make it to any of the suggested times. You start the whole process again, exchange a couple dozen emails, and somehow still have no date.

Good news! Thanks to awesome new technology—and to people committed to making calendaring less painful—there are plenty of tools that make planning easier and faster.

So, whether you cringe at the thought of having to move your appointments around to accommodate others or hate the idea of even pulling up the calendar and trying to find an available time, we’re sure that one of these three apps will be your new best friend.


1. Pick

GIF courtesy of Pick

When you’re scheduling a meetup, wouldn’t it be nice if you could skip the back-and-forth process and just check out the person’s calendar yourself? Pick makes this possible. While the app doesn’t tell you what your contact is doing at every moment of the day (because that’s just creepy), it does use intelligence to collect information from every participant’s Google Calendar.

That way, when you ask to meet with someone, Pick compares the calendars and only displays the times when all individuals are available.

Once a time is selected, Pick automatically adds the event to participants’ calendars and lets them know via email. And, if you’re scheduling a meeting with people who don’t have the app, you can easily share your availability with a personalized link so that your contact can select the time. While the app currently syncs with Google Calendar, the Pick team is working to support iCloud and Microsoft Exchange very soon.


2. Free

GIF courtesy of Free

If you’re in charge of planning office get-togethers, you know that tedious doesn’t begin to describe the process of finding a time when people are actually available (and don’t get me started on a menu that accommodates everyone). Even if you’re not usually the coordinator, you’ve probably been trapped in a huge group chat where no plans are solidified after 80 lines of messages.

That’s why Free was created—to make this planning process painless. At any time, you have three modes to choose from—Going Out, Flexible, or Busy. Then, Free forms groups from these statuses. Not only will you avoid bothering unavailable co-workers (or friends) because they won’t be placed in the group, but you also don’t have to choose a time that works for everyone because, well, every person in the group is already available.

And don’t worry about entering a group with complete strangers, because it’s up to you who can see your statuses, and who can join in on them. All of this, complete with features like tagging locations you’d like to go, “liking” friends’ suggested locations, and inviting new members into the chat.


3. Calendly

GIF courtesy of Calendly

Calendly is similar to Pick in its availability-sharing feature, but the app is particularly effective in scheduling recurring events. So, if your calendar is mostly filled with periodic weekly meetings instead of spontaneous coffee chats, this could be for you.

With this app, you set your availability preferences in a public Calendly page. Then, when you choose to share your Calendly page through a personalized URL, the invitees visit your page and select a time. And although Calendly only connects with your Google Calendar, the confirmed appointment will be added to your guests’ calendar—whether that’s Google, iCloud, or Outlook.

In addition to its beautiful interface, Calendly is useful in cloning your weekly agenda so that you don’t have to move your regular meetings in order to adjust to other people’s schedules. (It’s slightly selfish—but hey, you found Calendly first.)

Oh, and while the free plan allows for unlimited event scheduling, there is a premium plan at $8 a month that lets you create different event types and sends you automated reminders.



What apps or strategies do you use to make scheduling less painful? Let me know on Twitter!


Photo of calendar icons courtesy of Shutterstock.